CORYDALINE, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H27NO4
Molecular Weight	369.4541
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12[C@@H](C)C3=CC=C(OC)C(OC)=C3CN1CCC4=CC(OC)=C(OC)C=C24

InChI

InChIKey=VRSRXLJTYQVOHC-YEJXKQKISA-N

InChI=1S/C22H27NO4/c1-13-15-6-7-18(24-2)22(27-5)17(15)12-23-9-8-14-10-19(25-3)20(26-4)11-16(14)21(13)23/h6-7,10-11,13,21H,8-9,12H2,1-5H3/t13-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H27NO4
Molecular Weight	369.4541
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11809332 | https://www.ncbi.nlm.nih.gov/pubmed/20522959 | https://www.ncbi.nlm.nih.gov/pubmed/22689485

Corydaline is a pharmacologically active isoquinoline alkaloid isolated from Corydalis tubers. It exhibits the antiacetylcholinesterase, antiallergic, antinociceptive, and gastric emptying activities. Corydaline exhibited strong nematocidal activity, showed little cytotoxicity and represents a potential treatment for Strongyloidiasis. Corydaline exhibits gastrointestinal modulatory, antinociceptive, anti-allergic, and anti-parasitic activities. Corydaline is currently in clinical trials as a potential treatment for functional dyspepsia. In animal models, corydaline increases gastric emptying and small intestine transit speed and induces gastric relaxation. In other animal models, corydaline inhibits chemically-induced pain. Additionally, this compound may inhibit mast cell-dependent smooth muscle contraction of the aorta. Corydaline also exhibits nematocidal activity against species of Strongyloides.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
platelet aggregation 76 Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27558975	Inhibitor 8297
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17574358	Inhibitor 8297	15.0 µM [IC50]
Strongyloides ratti 3 Target ID: Strongyloides ratti Sources: https://www.ncbi.nlm.nih.gov/pubmed/11809332	Inhibitor 8297
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21826053	Inhibitor 8297	1.7 mM [Ki]
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21826053	Inhibitor 8297	7.0 mM [Ki]
Human enterovirus 71 3 Target ID: CHEMBL612436 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29034730	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Tachyarrhythmia 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22679741	Primary	Preclinical	Unknown Approved Use Unknown
Strongyloidiasis 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11809332	Primary	Basic research	Unknown Approved Use Unknown
Functional dyspepsia 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20522959	Primary	Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
2370 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CORYDALINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
419 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CORYDALINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
1123 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CORYDALINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
276 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CORYDALINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
34.7 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CORYDALINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
590.7 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CORYDALINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
324 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CORYDALINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
280 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CORYDALINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.327 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CORYDALINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
4.34% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CORYDALINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
6.26% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24216274	4.5 mg/kg single, oral dose: 4.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CORYDALINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

PubMed

Title	Date	PubMed
Formation of protoberberine-type alkaloids by the tubers of somatic embryo-derived plants of Corydalis yanhusuo.	2001 Dec	11745021
Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site.	2003 Apr	12709895
The combination of rat mast cell and rabbit aortic smooth muscle is the simple bioassay for the screening of anti-allergic ingredient from methanolic extract of Corydalis tuber.	2004 Aug	15305035
[Resource investigation and quality evaluation on wild Corydalis yanhusuo].	2004 May	15706885
Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg. & Kort.	2007 Aug 15	17574358
Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor.	2008 Sep 25	18830156
Rapid TLC/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts.	2008 Sep-Oct	18446766
Effects of corydaline from Corydalis tuber on gastric motor function in an animal model.	2010	20522959
Cytotoxic activity of proteins isolated from extracts of Corydalis cava tubers in human cervical carcinoma HeLa cells.	2010 Dec 17	21167042
Screening of antinociceptive components in Corydalis yanhusuo W.T. Wang by comprehensive two-dimensional liquid chromatography/tandem mass spectrometry.	2010 Mar	20101504

Patents

Sample Use Guides

In Vivo Use Guide

Corydaline was administered orally in a volume of 5 ml/kg for rats and 1 ml/kg for dogs.

Route of Administration: Oral

In Vitro Use Guide

Corydaline inhibited acetylcholinesterase in a dose-dependent manner with an IC(50) value of 15+/-3 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:16:44 GMT 2023` Edited by `admin` on `Sat Dec 16 09:16:44 GMT 2023`
Record UNII	6MUC9717YK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CORYDALINE, (±)-

Common Name

English

BERBINE, 2,3,9,10-TETRAMETHOXY-13.BETA.-METHYL-, (±)-

Systematic Name

English

(13SR,13ARS)-5,8,13,13A-TETRAHYDRO-2,3,9,10-TETRAMETHOXY-13-METHYL-6H-DIBENZO(A,G)-QUINOLIZINE

Systematic Name

English

6H-DIBENZO(A,G)QUINOLIZINE, 5,8,13,13A-TETRAHYDRO-2,3,9,10-TETRAMETHOXY-13-METHYL-, TRANS-(±)-

Systematic Name

English

(±)-CORYDALINE

Common Name

English

CORYDALINE DL-FORM [MI]

Common Name

English

NSC-298182

Code

English

6H-DIBENZO(A,G)QUINOLIZINE, 5,8,13,13A-TETRAHYDRO-2,3,9,10-TETRAMETHOXY-13-METHYL-, (13R,13AS)-REL-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID40975602